2-Fluoro-4-nitrophenol → 7-(2-Fluoro-4-nitrophenoxy)-2-(methylthio)thieno[3,2-b]pyridine

HRID 500862Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([S:11][CH3:12])[S:10][C:3]=12.[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[OH:23].C(=O)([O-])[O-].[Na+].[Na+]>C1(OC2C=CC=CC=2)C=CC=CC=1>[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[O:23][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([S:11][CH3:12])[S:10][C:3]=12

Participants

Conditions

Temperature: 200 °C

Procedure

To a suspension of 229 (100 mg, 0.463 mmol) in diphenyl ether (4 mL), was added 2-fluoro-4-nitrophenol (109 mg, 0.695 mmol) and sodium carbonate (147 mg, 1.39 mmol). The reaction mixture was heated atr 200° C. overnight, cooled to room temperature, loaded onto a flash chromatography column and eluted with EtOAc/hexane (1:1) to afford title compound 230 (0.135 mg, 86% yield) as a yellow solid. MS (m/z): 337.0 (M+1).

Workup

temperaturecooled to room temperature
washeluted with EtOAc/hexane (1:1)

Sources & evidence

ORD record: ord-9e006c840a2d45fcbf68aab16804701c
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772247B2

Reaction notes

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